The obsessive concern in Russian literary criticism with the national qualities of Russian literature in the second third of the nineteenth century has been traced in Russian literary historiography back into the 1820s and the debates over romanticism and narodnost’ (national originality). But the subject was broached publicly in the 1810s in debates that concerned translations as original and markedly Russian works of literature. While translation came to be seen as inimical to narodnost’ in the 1820s and 30s, it would return in a new form as a part of a generalized assimilative cultural project in the 1840s in Nikolai Gogol’s formulation of the nature and mission of the Russian nation. This paradoxical role played by translation, its function in the creation of original literature is, in both periods, linked to the work of Vasilii Zhukovskii. This article demonstrates how Zhukovskii’s practice as a translator, formed in the Friendly Literary Society of his youth and modeled after that of his friend Andrei Turgenev, evoked a critical response that engaged the newest concerns of Russia’s literary elite and generated new critical language and ideas through a productive mixing of classicist and romantic discourse on translations. Zhukovskii as an author-translator thus offers a rich case study to those interested in the creative aspect of translation.